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Preparation method of (E)-2-(2'-chloromethyl) phenyl-3-methoxy methyl acrylate

A technology of methyl methoxyacrylate and trimethyl orthoformate, which is applied in the field of preparation of methyl-2-phenyl-3-methoxyacrylate, can solve the problem of low total yield and the restriction of large-scale industrialization of fungicides Production and other issues, to achieve the effect of high total yield, low toxicity of reagents and drugs, and low synthesis cost

Active Publication Date: 2014-12-31
JIANGSU SEVENCONTINENT GREEN CHEM CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] According to literature reports, the traditional synthetic route of this intermediate is synthesized through 4 steps such as esterification, condensation, methylation and chlorination successively with anthranilic acid as the starting material, but due to the long route and the total The yield is low, which greatly restricts the industrialized large-scale production of related fungicides

Method used

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  • Preparation method of (E)-2-(2'-chloromethyl) phenyl-3-methoxy methyl acrylate
  • Preparation method of (E)-2-(2'-chloromethyl) phenyl-3-methoxy methyl acrylate
  • Preparation method of (E)-2-(2'-chloromethyl) phenyl-3-methoxy methyl acrylate

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Embodiment 1

[0021] Add 100 grams of 3-isochromone (1), 573 grams of trimethyl orthoformate and 120 grams of glacial acetic acid into a 1000ml round-bottomed flask, heat and reflux until the 3-isochromone (1) disappears, and remove the liquid to obtain intermediate To the crude product of body (2), add 300 grams of thionyl chloride, reflux reaction until the reaction of intermediate (2) is complete, add 200 grams of methanol, react at room temperature 25 ° C until the product is completely formed, stop the reaction, and dry by suction to obtain the product ( 3) 146 grams, yield 90%, purity 92%.

[0022] Product m.p:78-79℃. 1 H NMR (600MHz, DMSO-d 6 ):δ7.63(s,1H),7.52(m,1H),7.36(m,2H),7.10(s,1H),4.51(s,2H),3.84(s,3H),3.71(s, 3H).MS: m / z=240.3 (M + ).Anal.calcd for (C 12 h 13 ClO 3 ): C, 59.88; H, 5.44. Found: C, 59.68; H, 5.32.

Embodiment 2

[0024] Add 100 grams of 3-isochromone (1), 573 grams of trimethyl orthoformate and 120 grams of glacial acetic acid in a 1000ml round bottom flask, heat to reflux until 3-isochromone (1) (1) disappears, and remove the liquid , to obtain the crude product of intermediate (2), then add 1000 grams of thionyl chloride, reflux reaction until the reaction of intermediate (2) is complete, add 200 grams of methanol, react at room temperature 25 ° C until the product is completely formed, stop the reaction, and dry by suction filtration 154 g of product (3) was obtained with a yield of 95% and a purity of 94%.

Embodiment 3

[0026] Add 100 grams of 3-isochromone (1), 1166 grams of trimethyl orthoformate and 120 grams of glacial acetic acid into a 1000ml round-bottomed flask, heat and reflux until the 3-isochromone (1) disappears, remove the liquid, and obtain intermediate To the crude product of body (2), add 300 grams of thionyl chloride, reflux reaction until the reaction of intermediate (2) is complete, add 200 grams of methanol, react at room temperature 25 ° C until the product is completely formed, stop the reaction, and dry by suction to obtain the product ( 3) 149 grams, yield 92%, purity 95%.

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Abstract

The invention discloses a novel preparation method of (E)-2-(2'-chloromethyl) phenyl-3-methoxy methyl acrylate. The preparation method comprises the following steps: with 3-isochromanone as a starting material, under actions of trimethyl orthoformate and glacial acetic acid, performing condensation reaction to obtain an intermediate, and reacting the intermediate with thionyl chloride and methanol in sequence to obtain the (E)-2-(2'-chloromethyl) phenyl-3-methoxy methyl acrylate. According to the preparation method, the process is relatively simple, the raw materials are easy to obtain, the cost is low, the solid, liquid and gas wastes are few, and the content and yield of the target product are relatively high, and the method is suitable for industrial production.

Description

technical field [0001] The present invention relates to a kind of preparation method of (E)-2-(2'-chloromethyl)phenyl-3-methoxymethyl acrylate. Background technique [0002] (E)-2-(2'-chloromethyl)phenyl-3-methoxymethyl acrylate (3) is a key intermediate for the synthesis of methoxyacrylate fungicides, and its structural formula is as follows [0003] [0004] According to literature reports, the traditional synthetic route of this intermediate is synthesized through 4 steps such as esterification, condensation, methylation and chlorination successively with anthranilic acid as the starting material, but due to the long route and the total The yield is low, which greatly restricts the industrialized large-scale production of related fungicides. Therefore, it is urgent to find a more efficient and economical method for synthesizing (E)-2-(2'-chloromethyl)phenyl-3-methoxymethyl acrylate, thereby reducing its synthesis cost and realizing industrial production. This method ...

Claims

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Application Information

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IPC IPC(8): C07C69/734C07C67/08
CPCC07C67/08C07D311/76C07C69/734
Inventor 吴天宇何永利刘玉超陶伟金邦泰
Owner JIANGSU SEVENCONTINENT GREEN CHEM CO LTD